$116 Cheap flight deals from Chicago (CHI) to Portsmouth (BOS)

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This Weekend's Flight Deals from Chicago to Portsmouth

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 14 - Sat, Nov 21
ORD
O'Hare Intl.
BOS
Logan Intl.
$378 Roundtrip, found 12 hours ago
$378
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sat, Nov 14 from O'Hare Intl. to Logan Intl., returning Sat, Nov 21, priced at $378 found 12 hours ago

Airfares from $116 One Way, $227 Round Trip from Chicago to Portsmouth

Prices starting at $227 for return flights and $116 for one-way flights to Portsmouth were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Dec 22 - Sat, Jan 9
MDW
Chicago
BOS
Boston
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Dec 22 from Chicago to Boston, returning Sat, Jan 9, priced at $227 found 4 days ago
Wed, Dec 2 - Sat, Dec 5
ORD
Chicago
BOS
Boston
$238 Roundtrip, found 12 hours ago
$238
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Dec 2 from Chicago to Boston, returning Sat, Dec 5, priced at $238 found 12 hours ago
Wed, Jan 6 - Sat, Jan 9
ORD
Chicago
BOS
Boston
$245 Roundtrip, found 2 hours ago
$245
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Jan 6 from Chicago to Boston, returning Sat, Jan 9, priced at $245 found 2 hours ago
Fri, Jan 1 - Wed, Jan 6
ORD
Chicago
BOS
Boston
$246 Roundtrip, found 1 hour ago
$246
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Jan 1 from Chicago to Boston, returning Wed, Jan 6, priced at $246 found 1 hour ago
Wed, Dec 23 - Wed, Dec 30
MDW
Chicago
BOS
Boston
$247 Roundtrip, found 5 hours ago
$247
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Dec 23 from Chicago to Boston, returning Wed, Dec 30, priced at $247 found 5 hours ago

Portsmouth economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,636 reviews)

Dec 28 - Jan 1

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • Coach
Price was $906, price is now $670 per person
$670
per person
found 23 hours ago
Great service!

Reviewed on Nov 8, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,004 reviews)

Dec 11 - Dec 13

2 night stay

Chicago (MDW) to Boston (BOS)

Southwest Airlines • Coach

Boston (BOS) to Chicago (MDW)

Frontier Airlines • Coach
Price was $1,125, price is now $731 per person
$731
per person
found 1 day ago

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (343 reviews)

Dec 17 - Dec 20

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Price was $1,624, price is now $1,225 per person
$1,225
per person
found 21 hours ago
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

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More About Flying To Portsmouth from Chicago

Route Information for Flights from Chicago to Portsmouth

Origin Airport IATA Code
CHI
Destination Airport IATA Code
BOS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Portsmouth

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Frequently asked questions

Are there non-stop flights from Chicago to Portsmouth?
Direct flights are offered by no less than 4 airlines from Chicago, IL (ORD-O'Hare Intl.) to BOS, which means you could be booking your fun-filled getaway within moments. Here are some reputable carriers to consider:

  • United Airlines
  • American Airlines
  • Delta
  • JetBlue

What is the shortest flight from Chicago to Portsmouth?
The journey from Chicago to Portsmouth can be as fast as 2 hours and 59 minutes. With a leisurely flight time like this, why not organize an impromptu getaway?
What airlines fly from Chicago to Portsmouth most frequently?
Feed your wanderlust and travel with one of the following carriers that offer the most frequent flights from Chicago to Portsmouth: United Airlines - (UA) with 208 flights every month American Airlines - (AA) with 199 flights every month Delta - (DL) with 147 flights every month JetBlue - (B6) with 56 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.